To a methanolic solution of 4-isopropoxybenzaldehyde (0.93 g, 5.6 mmol) in methanol (20 mL) was slowly added a methanolic solution of sodium tetrahydroborate (0.32 g, 11 mmol) under cooling conditions in an ice bath. The reaction mixture was stirred at room temperature for 4 hours. Upon completion of the reaction, the reaction solution was acidified by adding 2N hydrochloric acid to the reaction solution and subsequently extracted with ether. The organic phases were combined, washed with water and concentrated under reduced pressure to remove the solvent. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate = 7:3) to afford the target product (4-isopropoxyphenyl) methanol (0.76 g, 81% yield) as a colorless oil.1H NMR (CDCl3) δ: 1.33 (6H, d, J = 6.1 Hz), 4.55 (1H, quintet, J = 6.1 Hz), 4.61 (2H, s), 6.85-6.91 (2H, m), 7.25-7.30 (2H, m).
